Step 1: Comprehending each measure.
- Mode: The most frequently occurring value in a dataset; the simplest measure.
- Mean: The average value of data; slightly more complex.
- Median: The central value when data is arranged in order; more resistant to outliers than the mean for skewed data.
- Range: The difference between the highest and lowest values; a straightforward description of data spread.
- Standard Deviation: Quantifies the dispersion of data points from the mean; the most complex measure of spread.
Step 2: Arranging them by complexity.
From least to most complex: (A) Mode $\rightarrow$ (B) Mean $\rightarrow$ (C) Median $\rightarrow$ (D) Range $\rightarrow$ (E) Standard Deviation.
Step 3: Confirming with provided options.
Option 2 accurately reflects this sequence.
Final Answer: \[\boxed{(A), (B), (C), (D), (E)}\]